Cytoskyrin C, an unusual asymmetric bisanthraquinone with cage-like skeleton from the endophytic fungus Diaporthe sp

Fitoterapia. 2018 Jul:128:253-257. doi: 10.1016/j.fitote.2018.05.032. Epub 2018 May 31.

Abstract

Cytoskyrin C (1), a new bisanthraquinone with asymmetrically cytoskyrin type skeleton, together with a known symmetrical analogue (+)-epicytoskyrin (2), were isolated from an endophytic fungus ARL-09 (Diaporthe sp.). Cytoskyrin C (1) featured an asymmetrically cage-like structural motif arising from the dimerization of anthraquinone monomers by three carbon‑carbon bonds 9a/3', 3/9a' and 1/1'. The structure and absolute configuration of compound 1 were determined by spectroscopic analyses, ECD calculation and exciton chirality methods. Moreover, a plausible biogenetic pathway of 1-2 was predicted. Their cytotoxicities against SMMC-7721 cell as well as effects on NF-κB signaling pathway were evaluated. 2009 Elsevier Ltd. All rights reserved.

Keywords: BisanthraquinonesNF-κB; Cytoskyrin; Cytotoxicity; Diaporthe sp..

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Ascomycota / chemistry*
  • Cell Line, Tumor
  • Endophytes / chemistry
  • Humans
  • Molecular Structure
  • NF-kappa B / metabolism
  • Orchidaceae / microbiology
  • Signal Transduction

Substances

  • Anthraquinones
  • NF-kappa B